James “Whitey” Bulger, who served as the inspiration for Jack Nicholson’s character in the 2006 film, The Departed, is on trial for racketeering as well as 19 murder charges. Bulger ran the infamous “Winter Hill” gang in South Boston during the 1970s and 1980s. Like Nicholson’s character in The Departed, Bulger was secretly informing the FBI while running his gang, and in 1994 after receiving a tip from a crooked FBI agent about his impending arrest, Bulger fled Boston and remained on the run until his 2011 arrest.
This guy is the kind of fascinating individual that seems better-suited for Hollywood than real-life. Whether through his depiction in The Departed or through his decade-long appearance on the FBI’s “10 Most Wanted” list, much of our nation’s population (especially in New England) has become enamored with Bulger. Today, as reported by Reuters, John Martorano, one of Bulger’s key hitmen, testified about Bulger’s murderous activity in great detail. Naturally after reading about the testimony, I went on an all-day information-gathering frenzy about Whitey. Yes this guy encouraged drug trafficking and killed many innocent people, but to me he’s a boss, and I’m not afraid to express this opinion because it has become commonplace in our society to revere or at least follow guys like Whitey. He’s fucked up and if people like him didn’t exist, our world would be safer and fairer. But criminals do exist and always will exist; therefore, those who were or are the best at it deserve some form of admiration. That’s why it’s Whitey’s turn to get the Philo-treatment, so here’s my list of his top 5 Boss moves (in chronological order):
In 1956, at age 27, Whitey was sentenced to serve prison time in the Atlanta Penitentiary for robbery and hijacking. He became involved in the MK-ULTRA program, which was a CIA operation focused on researching the effects of drugs using inmates as subjects. Basically, someone came up to Whitey and said, “Hey, we can reduce your sentence if you agree to try LSD and marijuana daily.” And White responded with something like, “Yeah bro, why the hell not? How much do I owe you?” Frat.
In 1959, Whitey was transferred from the Atlanta Penitentiary to Alcatraz. Not much to say about this one, besides the fact that anything Alcatraz-related is pretty badass. I feel like when you’re interviewing for a job in a gang, having Alcatraz on your resume is the criminal world version of Harvard Law School. Whitey attended Alcatraz on a full-scholarship and graduated with high honors.
3. First Murder
After “graduation,” Whitey joined the Killeen gang in Boston and quickly became involved in the Kileen-Mullen War of the early 1970s. In his novel, mob-boss Kevin Weeks, describes how Whitey sought out Mullen gang member, Paulie McGonagle:
“Jimmy pulled up beside him, window to window, nose to nose, and called his name. As Paulie looked over, Jimmy shot him right between the eyes. Only at that moment, just as he pulled the trigger, Jimmy realized it wasn’t Paulie. It was Donald, the most likable of the McGonagle brothers, the only one who wasn’t involved in anything. Jimmy drove straight to his mentor Billy O’Sullivan‘s house on Savin Hill Avenue and told O’Sullivan, who was at the stove cooking, ‘I shot the wrong one. I shot Donald.’ Billy looked up from the stove and said, ‘Don’t worry about it. He wasn’t healthy anyway. He smoked. He would have gotten lung cancer. How do you want your pork chops?'”
“How do you want your pork chops?” Fucking classic.
4. Cleaning Up The Hood
Although he was involved in marijuana and cocaine trafficking, Whitey forbid the sale of drugs to children, and he prevented PCP from entering his neighborhoods. This one is straight out of The Godfather.
5. Winning The Lottery
In 1991, Whitey raked in $14 million from winning the Massachusetts State Lottery. Sound sketchy? Yeah, it most certainly is sketchy. Bulger and his associates owned a South Boston liquor store, at which the winning lottery ticket was purchased. Whitey forced the winner to claim that he was partners with Bulger and 3 other gangsters, so that the 4 men could share the winnings. I’m not entirely sure how this didn’t seem a little suspicious to the lottery agency, or the Mass. government, but its ballsy as hell. Classic Whitey Move.